11 December 2023
This week's additions focus on leadership, strategy, and mindset, with new digests from Lenny's Podcast Product Career Growth, Cameron Herold, and Rob Walling. Highlights include Why VC money teaches spending, not the skill of making money Shutting an entire division is sometimes the highest-ROI decision available.
Showing 38 digests for 11 December 2023.
Jason Fried on bootstrapping, staying small, and building on instinct
Lenny's Podcast Product Career Growth
December 17, 2023
Bootstrapping
9
Business operating systems
8
Founder interviews
7
Why VC money teaches spending, not the skill of making money
Six-week appetite cycles replace estimates and kill runaway projects
Gut and instinct outperform data-driven decisions for most founders
Live coaching: scaling a multi-division events business past 30 people
Cameron Herold
December 17, 2023
Processes & SOPs
9
Management
8
Pivoting
6
Shutting an entire division is sometimes the highest-ROI decision available.
The PETA factor: pain and energy costs matter as much as P&L.
Growing five to seven key people is what takes a company to the moon.
How Matt Wensing sold his enterprise SaaS for eight figures in 12 years
Rob Walling
December 17, 2023
Case studies
10
Exit strategy
7
Pitching investors
6
Strategic positioning justified a high revenue multiple despite modest team size.
A 24-month inbound deal closed without a broker, using in-house M&A expertise.
Expect the world to slow your deal down — only shareholders want it to close.
Five rules for communicating like an executive
Dr. Grace Lee
December 17, 2023
Communication
8
Resilience & grit
7
Communication skill — not experience — drives who gets promoted
Frame every idea in terms of fiscal impact on the business
Senior roles mean more ambiguity; build internal certainty to thrive
AI strategy & adoption
YouTube
AI-driven operating systems: architecture, components, and security
Dylan Davis
December 17, 2023
AI strategy & adoption
9
Cybersecurity basics
7
Every traditional OS component has a direct LLM equivalent today
Autonomous agent swarms will replace step-by-step user prompting
Prompt injection demands a rethought security stack, not bolt-ons
Three mistakes killing your B2B SaaS landing page conversions
TK Kader
December 17, 2023
Vague hero copy loses visitors in milliseconds — be explicit.
Feature lists don't convert; benefits tied to differentiation do.
Buyers ignore fake trust signals; real testimonials and your face work.
Why most people don't grow on social media: attention, identity, and accountability
GaryVee
December 16, 2023
Social media
9
Identity & self-belief
8
Delegation
5
Platform diversification is why most creators plateau and stall
Reinvest early revenue into team, not lifestyle upgrades
Accountability over excuses: your outcomes are entirely self-determined
Resilience & grit
Podcast
Emotional regulation as the core skill of parenting and life
The Daily Stoic
December 16, 2023
Resilience & grit
8
Identity & self-belief
7
Rescuing kids from distress raises fragile adults who can't cope.
Trauma is the aloneness around hard moments — repair is always possible.
Separating who a child is from what they did changes everything.
How to tell better stories: Matthew Dicks on the craft of storytelling
Lenny's Podcast Product Career Growth
December 15, 2023
Copywriting
8
Public speaking
8
Pitching investors
6
Every good story hinges on one five-second moment of transformation.
Homework for life: recording daily moments builds an endless story vault.
In business, match theme not content — then snap a personal story into your point.
Business operating systems
YouTube
How to build a business operating system and become an automated CEO
Ryan Deiss
December 15, 2023
Business operating systems
10
Processes & SOPs
7
Delegation
6
Fast-growth companies fail at a 67% rate — more than the average business.
Franchises fail at only 15% because every franchise is an operating system.
Your goal: zero critical accountability bullets with your name on them.
Product-market fit
YouTube
How Figma's CPO thinks about product, design, and building things people love
EO
December 15, 2023
Product-market fit
9
Vision & mission
7
Communication
5
A PM's core job is storytelling, not shipping features
Ask 'why' five times before building what users request
The best products come from teams proud of their work, not metrics
Identity & self-belief
YouTube
How to overcome fear, build self-esteem, and stop caring what people think
GaryVee
December 15, 2023
Identity & self-belief
10
Resilience & grit
8
Motivation
6
Fear is fake — it collapses the moment you stop running from it.
Self-esteem is binary: secure people have nothing to lose by putting themselves out there.
Redefining success as peace of mind beats chasing urgency and stuff.
Five common SOP mistakes that make documentation useless
Layla at ProcessDriven
December 15, 2023
One SOP per path — mixing variations turns directives into option lists
Teams spend far more time reading SOPs than writing them
Link to a single source of truth instead of duplicating changeable facts
B2B startup metrics: revenue, retention, and gross margin
Y Combinator
December 15, 2023
Unit economics
9
Retention & loyalty
7
Business models
5
Revenue beats vanity metrics — GMV can hide a flatlined business.
Net dollar retention above 100% means cohorts grow without new sales.
Scale negative gross margin only after you have a plan to fix it.
Long-term planning
Podcast
Intel's AI strategy and the siliconomy with Pat Gelsinger
Masters of Scale
December 14, 2023
Long-term planning
9
AI strategy & adoption
7
Management
6
Why Intel sees Nvidia's AI lead as only innings one and two
Silicon supply chains are the new oil — geopolitics follow
Ask your four: where AI must go in your core business now